I’m only a gold, but have always been able to receive a 2pm checkout when asked, even in the past year. I’ve mostly been staying at limited service brands in the past year (Hampton, Honewood) without issue. I even received a 2pm checkout at the Doubletree Waikiki when staying on a non-qualifying travel zoo rate. Granted, I tend to need a late checkout about 50% of the time so I don’t always ask.